7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine as well as preparation method and application of 7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine
A technology of azole deoxyamino and nitrobenzene, which is applied in the field of medicine, can solve the problems of long reaction time, low sensitivity, and low yield, and achieve the effects of short synthetic route, simple operation, and high sensitivity
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[0026] Preparation part
[0027] The structure of the compound was obtained by H NMR spectroscopy ( 1 H NMR), carbon nuclear magnetic resonance ( 13 C NMR) and mass spectrometry (MS). Proton and Carbon NMR shifts (δ) are given in parts per million (ppm). Proton NMR spectrum is measured with Mercury-300, Mercury-400, Bruke-400 or Mercury-600 type nuclear magnetic resonance instrument, deuterated chloroform (CDCl 3 ) or heavy water (D 2 O) or deuterated dimethylsulfoxide (DMSO-d 6 ) as solvent and tetramethylsilane (TMS) as internal standard.
[0028] High-resolution mass spectrometry was determined by Agilent 1100series LC / MSD trap mass spectrometer or Theromo Exactive orbitrap plus LC / MSD mass spectrometer. Column chromatography generally uses 160-200 mesh silica gel as the carrier.
[0029] Anhydrous solvents were all worked up by standard methods. Other reagents were commercially available analytically pure.
preparation example 11
[0030] Preparation Example 1 Preparation of 1-amino 1-deoxy-glucose
[0031] The NBDG compound of the present invention starts from D-glucose, adopts known literature reports or publicly known feasible reaction methods in synthetic chemistry, and obtains appropriate derivatives as raw materials of the present invention.
[0032]
[0033] Scheme 1 reagents and reaction conditions: (NH 4 ) 2 CO 3 ,NH 3 h 2 O, EtOH, 80℃, 16h.
[0034] In a 100 mL sealed tube, 3.96 g of glucose monohydrate, 1.92 g of ammonium carbonate, 20 mL of ammonia, and 20 mL of ethanol were sequentially added. The mixture was heated to 80°C overnight, and the next day the reaction solution was cooled to room temperature, and the solvent was evaporated to obtain crude 1-amino-1-deoxyglucose, which was directly used in the next step.
[0035] Structural characterization of 1-amino-1-deoxyglucose
[0036]
[0037] Scheme 2 reagents and reaction conditions: Ac 2 O, pyridine, 0°C–25°C, 16h.
[0038] ...
Embodiment 1
[0039] Example 1 Preparation of 1-NBDG (1-[7-nitrobenzo-2-oxa-1,3-oxadiazole]amino-1-deoxyglucose)
[0040]
[0041] Scheme 3 reagents and reaction conditions: NBDCl or NBDF, K 2 CO 3 , DMF, 0℃–25℃, 16h.
[0042] In a 50 ml single-necked bottle, add 1 gram of NBDCl to 1 gram of crude 1-amino-1-deoxyglucose and 1 gram of potassium carbonate in 10 milliliters of DMF under ice-water bath conditions, stir at low temperature for 1 hour and gradually Return to room temperature. The reaction was detected by TLC until the reaction was completed, the solvent was evaporated, and the residue was purified by column chromatography (DCM:MeOH=50:1) to obtain the target product 1-NBDG (yield: <10%).
[0043] In a 50 ml single-necked bottle, add 1 gram of NBDF to 1 gram of 1-amino-1-deoxyglucose crude product and 1 gram of potassium carbonate in 10 ml of DMF solution under ice-water bath conditions, stir at low temperature for 1 hour and then gradually Return to room temperature. The r...
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